Trifluoroacetic acid → 2-[2-(3,5-Difluoro-benzylcarbamoyl)-propionylamino]-3-(1H-indol-3-yl)-propionic acid

HRID 2223250Notes

Reaction equation

HRID 2223250 reaction equation
C([O:5][C:6](=[O:35])[CH:7]([NH:18][C:19](=[O:34])[CH:20]([C:22](=[O:33])[NH:23][CH2:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[CH:26]=1)[CH3:21])[CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:32][C:27]1[CH:26]=[C:25]([CH:30]=[C:29]([F:31])[CH:28]=1)[CH2:24][NH:23][C:22]([CH:20]([CH3:21])[C:19]([NH:18][CH:7]([CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)[C:6]([OH:35])=[O:5])=[O:34])=[O:33]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 692836102-[2-(3,5-Difluoro-benzylcarbamoyl)-propionylamino]-3-(1H-indol-3-yl)-propionic acid tert-butyl ester

Product 1

HCID 692836132-[2-(3,5-Difluoro-benzylcarbamoyl)-propionylamino]-3-(1H-indol-3-yl)-propionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[2-(3,5-Difluoro-benzylcarbamoyl)-propionylamino]-3-(1H-indol-3-yl)-propionic acid tert-butyl ester (5.99 g, 12.3 mmol) was dissolved in dichloromethane (15 ml), and trifluoroacetic acid (15 ml) was added at 0° C. The mixture was stirred overnight at r.t. until all starting material was consumed (analytical HPLC). The volatiles were evaporated, the residue was taken up in ethyl acetate and washed with water. The organic layers were dried (Na2SO4). After evaporation of the solvent, the title compound, MS: m/e=429.4 (M+H+), (3.5 g, 66%) was obtained by chromatographic purification of the residue (silica gel, MeOH, CH2Cl2).

Workup

  1. customwas consumed (analytical HPLC)
  2. customThe volatiles were evaporated
  3. washwashed with water
  4. dry with materialThe organic layers were dried (Na2SO4)
  5. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-02c09472f2e7476b8021a4e4f117730d
Source dataset
uspto-grants-2008_05
Patent number
US07375099B2

Reaction notes

Loading…